Third party applications work on top of existing platforms that host users’ data. Although these apps access this data to provide users with specific services, they can also use it for monetization or profiling purposes. In practice, there is a significant gap between users’ privacy expectations and the actual access levels of 3rd party apps, which are often over-privileged. Due to weaknesses in the existing privacy indicators, users are generally not well-informed on what data these apps get. Even more, we are witnessing the rise of inverse privacy: 3rd parties collect data that enables them to know information about users that users do not know, cannot remember, or cannot reach. In this paper, we describe our recent experiences with the design and evaluation of Data-Driven Privacy Indicators (DDPIs), an approach attempting to reduce the aforementioned privacy gap. DDPIs are realized through analyzing user’s data by a trusted party (e.g., the app platform) and integrating the analysis results in the privacy indicator’s interface. We discuss DDPIs in the context of 3rd party apps on cloud platforms, such as Google Drive and Dropbox. Specifically, we present our recent work on Far-reaching Insights, which show users the insights that apps can infer about them (e.g., their topics of interest, collaboration and activity patterns etc.). Then we present History-based insights, a novel privacy indicator which informs the user on what data is already accessible by an app vendor, based on previous app installations by the user or her collaborators. We further discuss future ideas on new DDPIs, and we outline the challenges facing the wide-scale deployment of such indicators.